Isobutyraldehyde → HCID 57708859, compound

HRID 606513Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([Li])CCC.[CH:24](=[O:28])[CH:25]([CH3:27])[CH3:26].[Cl-].[NH4+]>C1COCC1>[OH:28][CH:24]([CH:25]([CH3:27])[CH3:26])[CH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4′-(methylsulfonyl)biphenyl-3-carbonitrile obtained in Reference Example 102 (2.00 g, 7.77 mmol) in THF (40 mL) was added dropwise n-butyllithium (1.6M hexane solution, 5.34 mL, 8.55 mmol) at −78° C., and the mixture was stirred at −78° C. for 1 hr. Isobutyraldehyde (1.06 mL, 11.7 mmol) was added to this solution at −78° C., and the mixture was further stirred at −78° C. for 3 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, and washed with saturated sodium chloride aqueous solution. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (25%-50% ethyl acetate/hexane) to give the title compound as a pale-yellow oil (1.66 g, 65%).

Workup

stirringthe mixture was further stirred at −78° C. for 3 hr
extractionthe mixture was extracted with ethyl acetate
washwashed with saturated sodium chloride aqueous solution
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (25%-50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-d6a82d78b58d4a2bb16f244711ed8add
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915267B2

Reaction notes

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